We Bike Tuscany

Recommended in
Lonely Planet Florence &
Tuscany travel guides
Val d'Orcia Dream Casual


To meet the needs of more budget-minded travelers, we've designed a "casual inns" version of one of our most popular tours. "Terra di Siena" is the magic, untouched part of Tuscany, and if you're into scenery, it's truly one of those places you have to "see before you die." The stuff of picture postcards and paintings, it is quintessential Toscana.

As you bike along solitary back roads your camera will be working overtime as each bend reveals a landscape more stunning and unreal than the last. And if that's not enough, the food and wine of this region is some of Italy's finest, and our "casual inns" version does not skimp here. You'll enjoy unrestricted menus (wine excepted) at, what we feel, are among the best trattorias of the area. Charming and authentic, we promise you will not feel deprived for this most important part of the tour!

Highlights of this trip include: wine tasting, pecorino cheese tasting, thermal baths in Bagno Vignoni. An off-the-beaten track adventure with a concentration of amazing and unforgettable rides.


$3380 per person

  • Duration: 4 days/3 nights
  • Distance traveled: 20-30 miles per day
  • Area: Val d'Orcia
  • Nearest city: Siena
  • Tour type: Road touring
  • Skill level: Intermediate
  • Season: April - October
  • Number of participants: 2-7
  • Minimum age: 15
  • Fully guided: yes
  • Support vehicles: yes
  • Transportation to start site: yes


Day 1

Pick up in Florence or in the Chianti and transfer to our inn in Sinalunga. Warm up ride in the afternoon for a first taste of the hills! Then enjoy welcome aperitifs in a typical osteria.

Dinner: Local restaurant
Accommodation: Charming casual inn

Day 2

Today's ride is one of our favorites. Lone cypresses, lunar landscape, golden ochre... You'll bike along solitary back roads on the edge of the hills, reaching the most enchanting villages and breathtaking spots of the region: Montisi and Trequanda. Unforgettable!

Dinner: Local restaurant
Accommodation: Charming casual inn

Day 3

Transfer day. Bold cypress trees line your route through the Val d'Orcia to the Pienza area. Enjoy a Pecorino cheese tasting at a farm along the way. Afterwards, head to Pienza for a visit of the town.

Dinner: Free night for dinner on your own
Accommodation: Charming casual inn

Day 4

Today a wonderful ride through the Senesi hills will take you to Bagno Vignoni, a medieval village founded by the Romans and famous for its hot spring water. A rewarding thermal bath after all that biking will make you feel like never before!


  • Pick up/drop off in Florence or surrounding area
  • Accommodations at 3 star inns
  • All breakfasts, one picnic lunch, cold drinks and snacks along the way
  • Two dinners with unrestricted menus, one free night for dinner on your own
  • Maps and detailed route directions
  • Van support and baggage transfers
  • Thermal bath
  • Wine tasting and pecorino cheese tasting
  • 27-speed high quality hybrid bikes, helmets, water bottles and handlebar bags
  • Small groups for personalized service


Please send us an email if you need more info. We will reply within 48 hours.